


Dudes Look Like...

by DragonOfChanges



Category: Supernatural
Genre: Abuse of Angelic Grace, Gen, Prostitution(sort of), cross dressing, lost bets
Language: English
Status: Completed
Published: 2016-07-07
Updated: 2016-07-07
Packaged: 2018-07-22 01:45:36
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 903
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7413727
Author URL: https://archiveofourown.org/users/DragonOfChanges/pseuds/DragonOfChanges
Summary: <blockquote class="userstuff">
              <p>Dean and Cas loose a bet to Sam. Inspired by that Aerosmith song.</p>
            </blockquote>





	Dudes Look Like...

“Sam, this is stupid.”

“So, you’re gonna chicken out, Dean? I won the bet, fair and square. Cas isn’t complaining about paying up.” Sam smiled wickedly at his brother. Dean glowered back at him, but said nothing. Never let it be said that Dean Winchester backs out of a bet. Ever. 

Just then Cas walked into the library. He had insisted on dressing for this… idiocy… on his own. Deans eyes went wide and his jaw dropped at the sight of the angel. The dark blue strapless dress came to mid-thigh, hinting at the garters beneath that held the lacy black stockings up on his freshly shaved legs. Three inch black heels accentuated his muscular calves, and the short brunette wig that topped it all off was styled to perfection. He had gone easy on the makeup, just enough to accentuate his cheekbones and his stunning blue eyes. Clip on earrings sparkled on his lobes.

“Cas. You look…wow.” Cas blushed.

“Thank you Dean. It took a while to get the makeup right, and walking in the heels took a bit of practice, but I think I did ok?” He looked at Sam for approval.

“Yeah, Cas. You did really good. Now go get dressed, Dean. Ask Cas if you need any help. And please shave- legs and face. The makeup won’t look right if you have a five o clock shadow.”

A little over an hour later they were ready to go. Dean wore a black dress similar to Cas’, with heels to match. He’d needed help with the wig and makeup, but he looked almost as good as Cas, if he did say so himself. His heels were only an inch, but it hadn’t taken him long to get the hang of walking in them. At Sams suggestion, Cas had used his Grace to put the final touches on the ensemble. Both were now a 36C bust, temporarily. They all walked out to the Impala. Instead of climbing in, Dean waited by the rear door, looking at Sam. Cas went to open it, but Dean stopped him, raising his eyebrows at his younger brothers questioning look.

“A gentleman opens the door for a lady, Sammy.” Sam rolled his eyes, but opened it for them, closing it once the 'ladies' had settled themselves. He straightened his tan blazer, dusted off his slacks, and climbed into the drivers seat. As they drove, Sam reminded them of the terms of fulfilling the bet.

“One walking pass up and down The Ave. No running. Smile. And remember who you ‘belong to’ tonight.”

“Yes, Sir.” Cas said softly. Dean scowled at him. 

“You see, Dean. Cas has the right attitude about all this” Dean said nothing, but continued to glower at the back of Sams head.

Finally, they hit the bottom end of The Ave (aka Hooker Row). Sam parked, and helped 'his ladies' from the car. Locking Baby up, he said “OK, show time, girls” His smug look irritated Dean. He was SO gonna get even with Sam for this.

On their walk, the other 'ladies of the evening' gave the trio a wide berth, since their 'owner' walked with them. They got the occasional jealous look, as well. They had gotten to the top end of the run without any trouble and were halfway back down when a very large man wearing biker leathers accosted Cas, grabbing his arm and pulling him close, then squeezing his ass. Cas startled at the unexpected grope, looking to Dean for help. He had no idea how to react in this situation.

“Hey, sweet cheeks, wanna have a good time?” The biker leered at Cas. Sam started to intervene, but Dean winked at his brother and sidled up to the biker.

“Hey, love.” he said in a sultry voice “It’s a two for one special today. I’m Deanna, and the lovely lady you have your hands on is Cassandra. How about the three of us wander off where its dark, and you let us show you a good time? Three hundred for both of us. Payable to Samuel, in the tan jacket.” The biker pulled out his wallet and quickly paid off Sam, who shot Dean a questioning look. Deans return gaze said ‘We got this’ so Sam pocketed the cash, and leaned on the building to wait. The biker put an arm around each of the ‘girls’, and they ducked down a nearby alley together. 

Two minutes passed, and there were sounds of a scuffle. A muffled shout. A thunk, and a soft curse. Then silence. Dean and Cas came out of the alley a moment later. Dean readjusted his dress, and huffed. He took a thick roll of bills that he had “liberated” from the biker, and stuffed it down his strapless bra. He walked up to Sam.

“OK, can we go home now?” Sam grinned widely.

“Sure.” He started walking back towards where the Impala was parked, Dean and Cas following behind. Sam laughed as a thought occurred to him.

“You know, if you two ever get tired of hunting, you could always…” Dean and Cas walked faster, flanking Sam, and hit him upside the head as they passed to either side of him. Sam yelped and rubbed his head. Cassandra and Deanna continued walking, and linked hands. They were positively strutting as they finished what Sam had meant to be a walk of shame.

**Author's Note:**

> Insert the usual non ownership disclaimers for characters and music here. Yada yada...


End file.
